The Neighbor across the street.
I couldn't say that we were jo buddies at all because I was too shy at the time to embrace it but I'm sure that the guy was a teaser. He's the kind of guy that is known for being a crazy mf, the kind of guy who gets drunk in a party and gets naked and goes running and jumps into the pool. He's not shy at all.
The first time I felt he was teasing me was one extremely hot evening of late summer when he invited me over to his house. He lived with his older brother in the little guest house at the back of their parents but that day he saw me from the window of his parents living room. He was already in his briefs when I got in. He was gaming on his old ps1 to some shooter game that I can't remember. He grabbed some cold beers, threw me one and almost hit me in my face and jumped onto the couch. I sat next to the guy and we talked while he played. I was kinda nervous: this guy is in his whities and I'm to close and I can see his dick print in his briefs and... I started to chub up. He rested the controller over his crotch and started to joke about how Dualshock could make him jizz his undies. He kept on joking and making it buzz and I was getting red. In fact I was sweating like a pig and now my cock was 3/4 hard.
Meanwhile we kept on talking some random shit and laughing and getting more and more drunk because beers and a humid heatwave are a perfect match. Suddenly he said he had to pee and took one of the cans, pulled his cock out thru the fly of his briefs and started to pee right there standing up next to the couch and giving me that weird look like "Look what I can do, do you like it dude?". I was like... 😶. He really gave a fuck about anything... we were friends but not that close. But we were drunk. He sat again letting all his weight collapse into the couch and kept on playing. His cock was not fully tucked in the fly but not hanging out either and I was lucky enough to be seated on the right side so I had the perfect angle to watch inside his briefs. It was like he was menacing to free itself of the fly and hang freely. Then he made the same joke again about the Dualshock. I was celebrating all his jokes because I was quite drunk by now. But he insisted in a way that made me think that maybe he was teasing me.
I leaned back in the couch and I could see how his cock was almost hanging out thru the fly and he kept doing that Dualshock thing and he started to get hard. My heart was racing and my cock got hard extremely quick. He joked about it and kept on playing with a hard on. He locked in his character against a wall of the level and started to shoot against it to make the controller vibrate. We were laughing but I was laughing nervously and I guess he knew it. His cock was cut, 7" (he told me so without me asking anything) quite thin and curved downwards. He even joked about having a pencil dick while flexing it.
We started to talk about sex while he kept on playing with his cock now hard as a rock sticking out like nothing happened. Then he looked at my basketball shorts and made a joke about me popping a tent. I was really excited. He was at this time stroking his hard cock and leaking a lot so he told me to take it out and I obliged. I pulled down my shorts and let my stiff cock out. He made some comments about my thickness and my length being me much more thicker and veiny. He put some porn on the tv and we started to officially jerk off. He suddenly grabbed my cock and started to jerk it and I almost lost it and jizz all over but I managed to hold back. He started to stroke his cock furiously and said "watch this" and he let go off his cock and nutted handsfree shooting like 4 or 5 ropes of cum down of his downward curved cock while laughing and I lost it and shoot like 6 ropes in my hand.
We cleaned all the mess and kept on talking about some random shit and laughing for an hour or so until we fell asleep in the couch. Like nothing happened.